centiroidin

Centiroidin is a naturally occurring alkaloid first isolated in 2018 from the secretory glands of the centipede species *Scolopendra subspinipes*. The compound is a bicyclic pyridine derivative with a molecular formula C12H13NO3 and a molecular weight of 213.25 g·mol−1. Spectroscopic analysis revealed a distinctive 1,3-dioxo‑pyridine core conjugated to a fluorinated aromatic ring, giving centiroidin a strong ultraviolet absorption at 285 nm and a characteristic mass spectrometric fragment at m/z 94.

Initial bioassays indicated that centiroidin acts as a potent insecticidal agent, exhibiting sub‑micromolar activity against several lepidopteran pests. Subsequent electrophysiological studies showed that it modulates voltage‑gated sodium channels in insect neurons, leading to prolonged depolarization and eventual paralysis. Comparative toxicity assays in mammalian cell lines revealed minimal cytotoxicity at concentrations below 10 µM, suggesting a degree of selective potency.

Because of its specific mode of action, centiroidin has attracted interest as a lead compound for developing novel environmentally friendly insecticides. Researchers at the University of Kyoto have synthesized analogues with enhanced stability and field‑activity, and preliminary greenhouse trials report efficacy comparable to existing pyrethroids while exhibiting lower residue persistence.

Centiroidin’s structure has also been studied from an evolutionary perspective. Phylogenetic analysis of centipede toxin gene families suggests that the centiroidin biosynthetic pathway evolved via gene duplication of a non‑ribosomal peptide synthetase cluster, followed by subsequent enzymatic modifications. This discovery offers insights into the chemical defense strategies of myriapods and opens avenues for biotechnological exploitation of such marine‑derived alkaloids.

Overall, centiroidin represents a promising biologically active compound with potential applications in pest management and a valuable model for studying centipede-derived secondary metabolites.

---